Ethylamine → HCID 86669831, compound

HRID 1620270Notes

Reaction equation

Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:16])=[C:7]([O:14][CH3:15])[CH:8]=2)[N:3]=1.[CH2:17]([NH2:19])[CH3:18]>C1COCC1>[CH2:17]([NH:19][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:16])=[C:7]([O:14][CH3:15])[CH:8]=2)[N:3]=1)[CH3:18]

Participants

Conditions

Temperature: 150 °C

Procedure

To a stirred solution of 2-chloro-7-fluoro-6-methoxyquinoline-3-carbaldehyde SMA 44034 (219 mg, 0.91 mmol) in THF (10 mL) in a 20 mL microwave vial equipped with a magnetic stirrer was added ethylamine (2 M in THF, 4.50 mL, 9.00 mmol) and the mixture was stirred at 150° C. for 2 h under microwave irradiation. After cooling to RT, the volatiles were removed under vacuum at 40° C. and the resulting yellow oil was taken up in a 2 N aq. HCl solution (15 mL) and stirred for 15 min at RT then neutralised with a 2 N aq. NaOH solution (15 mL). The mixture was extracted with CH2Cl2:MeOH=9:1 (50 mL) and the organic phase was washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated at 40° C. under vacuum. Purification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 75:25) gave 2-(ethylamino)-7-fluoro-6-methoxyquinoline-3-carbaldehyde CCH 42068 as a yellow oil (105 mg, 46% yield).

Workup

temperatureAfter cooling to RT
customthe volatiles were removed under vacuum at 40° C.
stirringstirred for 15 min at RT
extractionThe mixture was extracted with CH2Cl2
washMeOH=9:1 (50 mL) and the organic phase was washed with brine (10 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated at 40° C. under vacuum
customPurification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 75:25)

Sources & evidence

ORD record: ord-3b1f0994461645be98d90656858eac30
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772316B2

Reaction notes

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